Life-Altering Questions Answered By People Who Seemingly Have It Together

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Life-Altering Questions Answered By People Who Seemingly Have It Together

In the past few months, I have written about relationships, careers, how to make it all work… and what happens when it all shits the bed. Over the course of this time, I have enjoyed seeing your reactions and insights, be they emails, Tweets, article comments, or jaunty gifs worth well-beyond a thousand words.

Often, there was a request for advice on taking what was presented a step beyond, or perhaps a different angle. Here’s to keeping the “Problems” in Post Grad Problems.

Hey Caroline,

So I’ve been struggling with what I want lately as far as how I’m living my life and was thinking you might be able to give me some advice. Four months ago, I thought the beginning of 2016 was when I was going to propose to my girlfriend of three years and start my journey of settling down, getting married, and starting a family. I was ready and excited to do all of these things. Then my girlfriend broke up with me for another guy and I found myself a single, 23 year old that wanted all of these things that I was now miles away from. Many of my friends have encouraged me to just enjoy being young, partying, and being single, but switching to that lifestyle is hard to wrap my mind around. It almost seems like going backwards to me. I want to get back out there and find a serious relationship again, but for the time being I still live in the college town I went to school in (my ex was finishing professional school) and the girls I meet aren’t really what I’m looking for. I also feel like I have no clue how to date in today’s world. Essentially, I’m just struggling with whether or not I should just let loose and enjoy being young and single or if I should get back out there and try to get back on the path I was on. Any advice?

Newly Single and Struggling


First, I am so sorry about the painful shock you have endured over these past few months. I can imagine how hurtful and startling it was.

Your friends have your best interest at heart; we never like to see those we care about suffering and I am glad you have a good support system in place.

I always encourage anyone I work with to look back at their own values. Your 23-year-old friends may very well LOVE the bar, Bud Light, and Bumble life. And you’re their friend, so I am sure they’d LOVE your company on these exploits in addition to the assumed knowing that these kinds of experiences would be helping you heal.

But that doesn’t mean the lifestyle their espousing needs to be for you. If this direction does not align for you, there is no need to take it simply because of how many candles were on your last birthday cake. Others, while they mean well and care about us, aren’t the ones living our lives and experiencing our decisions- we are.

How to date in today’s world? Listen and be yourself above all. My friend and fellow writer, Winger wrote a good piece on dating apps a few months ago.

Personally, for your needs, I’d like to add to the list. It’s been around a while and is known for attracting people looking for something more on the serious side. Some people cannot imagine settling down in their early twenties, others swear it was the best thing they ever did. My brother and sister both were married to their respective spouses at 24 and are happily still so today. I couldn’t have imagined such a feat at that age. You will find countless anecdotes on both sides. They only story that matters is yours. Do what feels good and take care of yourself.


About six months ago I got out of a toxic three year on again off again relationship and moved from my hometown to a bigger city (admittedly only a four hour drive down the interstate and I already had friends in this town, but something I have always wanted to do), so a lot of changes!

One of my good friends here in the city is engaged to my ex bf’s very best friend, dating back to elementary days. I have always made a point that she knows I would never ask her to take a side or bash my ex since she is marrying his best friend and that’s a tough spot for her to be in.

The issue is, how things ended with him were particularly hurtful for me and even after six months I get upset when I see her posting things on social media of them all hanging out together. I cannot and will not ask her to stop posting things or hanging out with him, but I’m not sure I will ever be cool with seeing pictures of him spending time with my friends. At least not for some time.

Truthfully, I just want to move on with my life and forget about him, but I can’t do that with a Snapchat live stream of his life. Am I being a big baby about this? How do I proceed?

Scared of Social

Dear SOS,

You will one day be super cool with seeing pictures of him spending time with your friends—even if it was on a billboard in Times Square during the New Year’s Eve broadcast—I promise you; they day will come sooner than you think.

I thought about your letter when I was at yoga on Sunday. I was laying on my side and I was facing the glass door of the yoga studio that looks out into one of the cardio sections of the gym. In my view was the line of about eight or nine TV screens that face the treadmills — all flashing various images, all demonstrative of competing sources vying for our attention.

It was tempting to be distracted—but I just chose not to look and subsequently get sucked in. You are correct — you cannot preside over your friend’s social media posting habits as your ex is a genuine and beloved part of her life.

The only part you can control or change is how you consume this media. You can ask your friend to be a little more conscious of you in the wake of your deep hurt and not send you the Snaps of them together (weird that she does). You can also adjust your settings to control what you see in your newsfeed. If she’s one of your best friends, you can trust you won’t miss anything big in her life because you didn’t see it on Facebook with the rest of the masses.

One of my friends got engaged last week, one got pregnant. They both called me. I am not sure how the kids do it today, but I am sure there is still a “Priority Access Lane” when it comes to sharing information with close friends.

There are also a ton of apps that will collapse all of your Facebook newsfeed so it does not show up at all. So then yes, you’d have to go looking for these images—and I hope you’re not that much of a masochist.

Also, I will be the first to tell you that social media hiatus is easier to do than you think. I did one this summer. It was refreshing to seek out the news each morning from a reputable outlet and consciously connect with friends and family without the prompting of apps. Yes, my finger would phantom hover above the Facebook or Instagram icons the first few days, but it was gone shortly thereafter. Overall, it was an energizing experience I’d recommend to anyone.

The best way to forget about your ex is to live your life—away from the computer / phone / tablet screen. I wrote something that may help you with this back in November — feel free to check it out here.

You are the guardian of what gets in your brain. There are many ways to control what is worthy of your attention and energy. You have the power — don’t be afraid to use it!

Hello Caroline,

My name is Eve. I enjoyed reading your article ‘The Second Awkward Stage for Adults.’ I am 23 years old and will have been graduated from college for 2 years this year. I definitely feel I am at an awkward time because in Nov 2014, I was broken up with after 5 years by my boyfriend at the time. It was devastating to be a new grad, starting work in the real world, and having to deal with heart break on top of it.

It’s been a year and 2 months since my break-up, and I feel better than I have in a long time. I feel free, strong, resilient, and more. Sometimes I’m set back though because pretty much all of my friends are married, in serious relationships, or engaged. It’s weird to not be part of that world anymore. I am slowly gaining some single friends which has helped. I was wondering still how to deal with being the only single friend among friends who are in relationships.


Hi Eve,

I am happy to hear you are feeling better; that is great news.

I understand how being around happy couples can chafe at your sore spot after a major break-up. Additionally, the logistics aren’t always in your favor when you feel like you are third, fifth, or even seventh (I’ve done it!) wheeling. Sometimes, our perceptions of being the only single one are much stronger –we stick ourselves under the microscope and think everyone is noticing we’re the only ones unaccompanied when the truth is—they’re not noticing. They are just enjoying our company for who we are, regardless of whether we are a convenient unit of two conducive to dinner party seating. So my first piece of advice is to relax there.

You are 23, so my guess is in the words of America’s most famous mermaid, you will soon be “part of that world” again. This feeling is not permanent. However, having been on both sides now, you will come out stronger than ever.

While we are on a #TBT streak with our friend Ariel, I will continue it. I did a brief stint in the Girl Scouts in the early 90s. We learned to weave wallpaper samples together to sit on at camp (these are called “sit-upons”), but we also learned this fire jam — “Make new friends, but keep the old. One is silver and the other’s gold.”

A girl needs both in her life, right? I am glad to hear you are already in this process. I am married, and I admit sometimes I just cannot hang with my single friends. Though I love them, we just want different things. This goes both ways. I sometimes thought married people were boring AF when I was single (still do sometimes, actually).

You can really focus on cultivating those fellow single friends. A great way to do this is to play hostess. Organize and outing, throw a little party at your house. Don’t be afraid to ask a cool chick to get coffee, a cocktail, etc. It’s like any other date—you may feel awkward but the recipient will probably feel quite flattered.

It sounds like you have a great balance of old, tried and true friends who know you and your history plus some exciting new people to dress up and go out with on the weekend. I think you’re in a good place. Keep ya head up.

Having your own awkward stage, awkward moment, or just plain in a bind or rut? I want to hear about. I don’t know everything, but I can help you listen to yourself better. Get at me here. All submissions will be kept anonymous.

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